Fungicidal pyrimidinones

Details Fungicidal pyrimidinones Fungicidal pyrimidinones

1998-01-02

2000-05-23

Raymond, Richard L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514 63, 514248, 514249, 514259, 514262, 514267, 544229, 544236, 544237, 544249, 544255, 544256, 544257, 544258, 544265, 544278, 544279, 544280, 544284, 544285, 544287, 544290, A61K 31505, C07D49304, C07D49504

Patent

active

060666382

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to certain pyrimidinones, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
DT 2,210,503, DT 2,411,274, DT 2,411,273, and DD-A-240,892 disclose certain thienopyrimidine compounds. These publications, however, do not disclose the compounds of the present invention nor agricultural fungicide utility. U.S. Pat. No. 3,755,582 and U.S. Pat. No. 3,867,384 disclose certain 4(3H)-quinazolinone fungicides. These publications, however, do not disclose the compounds of the present invention.


SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides: ##STR2## wherein W is O, S(O).sub.n or NR.sup.5 ; thiazole, oxazole, imidazole, pyrazine, pyridazine or pyrimidine ring; -C.sub.10 alkenyl; C.sub.3 -C.sub.10 alkynyl; C.sub.1 -C.sub.10 haloalkyl; C.sub.3 -C.sub.10 haloalkenyl; C.sub.3 -C.sub.10 haloalkynyl; C.sub.2 -C.sub.10 alkoxyalkyl; C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.2 -C.sub.10 alkylsulfonylalkyl; C.sub.4 -C.sub.10 cycloalkylalkyl; C.sub.4 -C.sub.10 alkenyloxyalkyl; C.sub.4 -C.sub.10 alkynyloxyalkyl; C.sub.4 -C.sub.10 alkenylthioalkyl; C.sub.4 -C.sub.10 alkynylthioalkyl; C.sub.2 -C.sub.10 haloalkoxyalkyl; C.sub.4 -C.sub.10 alkoxyalkenyl; C.sub.4 -C.sub.10 alkylthioalkenyl; C.sub.4 -C.sub.10 trialkylsilylalkyl; C.sub.1 -C.sub.10 alkoxy; NR.sup.6 R.sup.7 ; R.sup.11 ; phenyl, pyridinyl, furanyl, thienyl, naphthalenyl, benzofuranyl, benzo[b]thiophenyl or quinolinyl each optionally substituted with R.sup.8, R.sup.9 and R.sup.10 ; or C.sub.1 -C.sub.10 alkyl substituted with NR.sup.6 R.sup.7, nitro, cyano, CO.sub.2 R.sup.6, or phenyl optionally substituted with R.sup.8, R.sup.9 and R.sup.10 ; -C.sub.10 alkenyl; C.sub.3 -C.sub.10 alkynyl; C.sub.1 -C.sub.10 haloalkyl; C.sub.3 -C.sub.10 haloalkenyl; C.sub.3 -C.sub.10 haloalkynyl; C.sub.2 -C.sub.10 alkoxyalkyl; C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.2 -C.sub.10 alkylsulfonylalkyl; C.sub.4 -C.sub.10 cycloalkylalkyl; C.sub.4 -C.sub.10 alkenyloxyalkyl; C.sub.4 -C.sub.10 alkynyloxyalkyl; C.sub.4 -C.sub.10 alkenylthioalkyl; C.sub.4 -C.sub.10 alkynylthioalkyl; C.sub.2 -C.sub.10 haloalkoxyalkyl; C.sub.4 -C.sub.10 alkoxyalkenyl; C.sub.4 -C.sub.10 alkylthioalkenyl; C.sub.4 -C.sub.10 trialkylsilylalkyl; R.sup.11 ; phenyl optionally substituted with R.sup.8, R.sup.9 and R.sup.10 ; or C.sub.1 -C.sub.10 alkyl substituted with NR.sup.6 R.sup.7, cyano, nitro, CO.sub.2 R.sup.6, or phenyl optionally substituted with R.sup.8, R.sup.9 and R.sup.10 ; or --OR.sup.7 ; --N.dbd.CR.sup.6 R.sup.6 ; --NR.sup.6 R.sup.7 ; and pyridinyl, furanyl, thienyl and naphthalenyl each optionally substituted with R.sup.8, R.sup.9 and R.sup.10 ; or --N.dbd.CR.sup.6 R.sup.6 and --NR.sup.6 R.sup.7 ; cycloalkyl; C.sub.2 -C.sub.8 alkenyl; C.sub.2 -C.sub.8 alkynyl; C.sub.1 -C.sub.8 haloalkyl; C.sub.3 -C.sub.8 haloalkenyl; C.sub.3 -C.sub.8 haloalkynyl; C.sub.1 -C.sub.8 alkoxy; C.sub.1 -C.sub.8 haloalkoxy; C.sub.3 -C.sub.8 alkenyloxy; C.sub.3 -C.sub.8 alkynyloxy; C.sub.1 -C.sub.8 alkylthio; C.sub.1 -C.sub.8 alkylsulfonyl; C.sub.2 -C.sub.8 alkoxyalkyl; C.sub.3 -C.sub.8 trialkylsilyl; nitro; NR.sup.6 R.sup.7 ; C.sub.5 -C.sub.8 trialkylsilylalkynyl; or phenyl optionally substituted with at least one R.sup.13 ; haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy; optionally substituted with at least one R.sup.13 ; op

REFERENCES:
patent: 3021332 (1962-02-01), Hitchings et al.
patent: 3749724 (1973-07-01), Wiedemann et al.
patent: 3755582 (1973-08-01), Bullock
patent: 3794637 (1974-02-01), Wiedemann et al.
patent: 3804835 (1974-04-01), Wiedemann et al.
patent: 3867384 (1975-02-01), Bullock et al.
patent: 3931183 (1976-01-01), Hardtmann
patent: 4925843 (1990-05-01), Takahashi et al.
patent: 5034393 (1991-07-01), Hackler et al.
patent: 5753664 (1998-05-01), Aono et al.
Sauter et al. Chemical Abstracts, 136088 q., vol. 81, 1974.
F. Sauter et al., Monatshefte fur Chemie 104, 1593-1598 (1973) by Springer-Verlag, Synthese von 2-Mercapto-thieno[2,3-d]pyrimidin-4(3H)-on-Derivaten.
Sauter et al., Chemical Abstracts, 82868c, vol. 80, 1973.
F. Sauter et al., Moatshefte fur Chemie 105, 863-868 (1974) by Springer-Verlag, Synthese von 2-Methylen-2,3-dihydro-und 2-Methyl-5H-thiazolo[3,2-a]pyrimidinen.
Chemical Abstracts 19850m, vol. 110, 1989.
Sugiyama et al., Condensed Thienopyrimidines. II. Synthesis and Gastric Antisecretory Activity of Thiazole and Polymethylene Condensed Thienopyrimidine Derivatives, Chem., Pharm. Bull. 37(8) 2122, pp. 2122-2131, vol. 37, No. 8, 1989.
Quijano M L et al., Synthesis and anticancer and antimicrobial activities of pyrrolo[2,3-d]pyrimidines, J. Heterocycl. Chem., 27(4), 1079-83, 1990.
Okamoto et al., Bull. Chem. Soc. Jpn., 59 (6), 1915-19, 1986.
Kondo et al., Chem. Lett., 80 (5), 559-62, 1980.
Talukdar et al., Indian J. Chem. Sect. B, 22B (3), 243-8, 1983.
Reichman et al., J. Chem. Soc., Perkin Trans. 1, 73 (22), 2647-55, 1973.
Seela et al., J. Med. Chem., 27 (8), 981-5, 1984.
Chemical Abstracts, 75, No. 5, Abstract 34976 (Ul'Yanova et al.), 1971.
Chemical Abstracts, 64, No. 7, Abstract 9725a (Nikolaeva), 1966.
El-Feky et al., Egypt. J. Pharm. Sci., 35 (1-6), 246, 1994.
Shukla et al., Indian J. For., 7 (2), 153, 1984.
Mittra et al., Acta Cienc. Indica., 9 (1-4), 109-12, 1983.
Das et al., J. Indian Chem. Soc., 56 (4), 398-400, 1979.
Dave et al., J. Inst. Chemist (India), vol. 57, Jul. 1985, pp. 156-158.
Translation of East German Patent No. 240892A, Nov. 19, 1986.
Urleb et al., The Synthesis and Transformations of 3-Ethoxycarbonyl-2-isothiocyanato-pyridine, Pyrido[2,3-d]pyrimidines and Some Azolopyrido[2,3-d]pyrimidines. J. Heterocyclic Chem., vol. 27, pp. 643-646, Mar.-Apr. 1990.
Urleb et al., The Synthesis and Transformations of 2-Ethoxycarbonyl-3-Isothiocyana-topyridine. Pyrido[3,2-d]pyrimidines and some Azolopyrido[3,2-d]pyrimidines. J. Heterocyclic Chem., vol. 27, pp. 407-412, Feb. 1990.
Urleb et al., The Reaction of 2-Ethoxycarbonyl-3-isothiocyanatopyridine with a-Amino Acids. The Synthesis of 3-Substituted 2-Thiooxo-2,3-dihydropyrido[3,2-d]pyrimidin-4(3H)-ones, J. Heterocyclic Chem., pp. 413-415, vol. 27, Feb. 1990.
Prameela B., et al., Synthesis and Antifungal Activity of Isoxazolylquinazolin-4(3H)-ones, Indian Journal of Heterocyclic Chemistry, 2, 115-118, 1992.
Abstract, HU 62757-T, Fungicide--Comprising Quinazoline Derivative, C2 Heterocyclic, eek 9332, 6, 1993.

Affiliated with

Also associated with

Rating

Fungicidal pyrimidinones does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Fungicidal pyrimidinones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fungicidal pyrimidinones will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1837271